Bioinspired Syntheses of the Marine Pyridoacridine Alkaloids 2-Bromo and 3-Bromodeoxyamphimedine and Structure Correction of 2-Bromoamphimedine.
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| Formato: | Artículo científico |
| Lenguaje: | en |
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Journal of natural products
2025
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| author | Blyth, Nathan Chen, Yi Rouvier, Florent Brunel, Jean Michel Cadelis, Melissa M Copp, Brent R |
| author_facet | Blyth, Nathan Chen, Yi Rouvier, Florent Brunel, Jean Michel Cadelis, Melissa M Copp, Brent R Blyth, Nathan Chen, Yi Rouvier, Florent Brunel, Jean Michel Cadelis, Melissa M Copp, Brent R |
| collection | PubMed - marine biology |
| contents | Bioinspired Syntheses of the Marine Pyridoacridine Alkaloids 2-Bromo and 3-Bromodeoxyamphimedine and Structure Correction of 2-Bromoamphimedine. Blyth, Nathan Chen, Yi Rouvier, Florent Brunel, Jean Michel Cadelis, Melissa M Copp, Brent R Animals Acridines Alkaloids Anti-Bacterial Agents Biological Products Marine Biology Molecular Structure Oxidation-Reduction Porifera Phenanthrolines We have used an efficient bioinspired methodology to synthesize, for the first time, the recently reported antibacterial brominated pyridoacridine alkaloids 2-bromodeoxyamphimedine and 3-bromodeoxyamphimedine. The synthetic route started with the synthesis of 5-bromo and 6-bromokynuramine, the latter being a sponge-derived marine natural product. Oxidative addition of the brominated kynuramine analogues, with Boc-dopamine, afforded the anticipated natural products 2- and 3-bromostyelsamine D. Further Pictet-Spengler reaction with paraformaldehyde afforded the target brominated deoxyamphimedines, spectroscopic data for which were in excellent agreement with those reported for the isolated natural products. Oxidation of 2-bromodeoxyamphimedine and 3-bromodeoxyamphimedine using K[Fe(CN)] gave 2- and 3-bromoamphimedine, respectively. H NMR data reported for '2-bromoamphimedine', isolated from a n. sp. sponge differed from the data observed for synthetic 2-bromoaphimedine but were in good agreement with those observed for synthetic 3-bromoamphimedine, requiring structure correction of the isolated natural product. |
| format | Artículo científico |
| id | pubmed_40674171 |
| institution | PubMed |
| language | en |
| publishDate | 2025 |
| publisher | Journal of natural products |
| record_format | pubmed |
| spellingShingle | Bioinspired Syntheses of the Marine Pyridoacridine Alkaloids 2-Bromo and 3-Bromodeoxyamphimedine and Structure Correction of 2-Bromoamphimedine. Blyth, Nathan Chen, Yi Rouvier, Florent Brunel, Jean Michel Cadelis, Melissa M Copp, Brent R Animals Acridines Alkaloids Anti-Bacterial Agents Biological Products Marine Biology Molecular Structure Oxidation-Reduction Porifera Phenanthrolines Bioinspired Syntheses of the Marine Pyridoacridine Alkaloids 2-Bromo and 3-Bromodeoxyamphimedine and Structure Correction of 2-Bromoamphimedine. Blyth, Nathan Chen, Yi Rouvier, Florent Brunel, Jean Michel Cadelis, Melissa M Copp, Brent R Animals Acridines Alkaloids Anti-Bacterial Agents Biological Products Marine Biology Molecular Structure Oxidation-Reduction Porifera Phenanthrolines We have used an efficient bioinspired methodology to synthesize, for the first time, the recently reported antibacterial brominated pyridoacridine alkaloids 2-bromodeoxyamphimedine and 3-bromodeoxyamphimedine. The synthetic route started with the synthesis of 5-bromo and 6-bromokynuramine, the latter being a sponge-derived marine natural product. Oxidative addition of the brominated kynuramine analogues, with Boc-dopamine, afforded the anticipated natural products 2- and 3-bromostyelsamine D. Further Pictet-Spengler reaction with paraformaldehyde afforded the target brominated deoxyamphimedines, spectroscopic data for which were in excellent agreement with those reported for the isolated natural products. Oxidation of 2-bromodeoxyamphimedine and 3-bromodeoxyamphimedine using K[Fe(CN)] gave 2- and 3-bromoamphimedine, respectively. H NMR data reported for '2-bromoamphimedine', isolated from a n. sp. sponge differed from the data observed for synthetic 2-bromoaphimedine but were in good agreement with those observed for synthetic 3-bromoamphimedine, requiring structure correction of the isolated natural product. |
| title | Bioinspired Syntheses of the Marine Pyridoacridine Alkaloids 2-Bromo and 3-Bromodeoxyamphimedine and Structure Correction of 2-Bromoamphimedine. |
| topic | Animals Acridines Alkaloids Anti-Bacterial Agents Biological Products Marine Biology Molecular Structure Oxidation-Reduction Porifera Phenanthrolines |
| url | https://pubmed.ncbi.nlm.nih.gov/40674171/ |